PL125030B1 - Method of manufacture of novel derivatives of 4-aminoquinoline-3-carboxylic acid - Google Patents
Method of manufacture of novel derivatives of 4-aminoquinoline-3-carboxylic acid Download PDFInfo
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- PL125030B1 PL125030B1 PL1980222993A PL22299380A PL125030B1 PL 125030 B1 PL125030 B1 PL 125030B1 PL 1980222993 A PL1980222993 A PL 1980222993A PL 22299380 A PL22299380 A PL 22299380A PL 125030 B1 PL125030 B1 PL 125030B1
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- Poland
- Prior art keywords
- ethyl ester
- title compound
- preparing
- amino
- preparation
- Prior art date
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- 238000000034 method Methods 0.000 title description 80
- 238000004519 manufacturing process Methods 0.000 title description 58
- UEFKMJWKPVAVND-UHFFFAOYSA-N 4-aminoquinoline-3-carboxylic acid Chemical class C1=CC=C2C(N)=C(C(O)=O)C=NC2=C1 UEFKMJWKPVAVND-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 description 194
- 238000002360 preparation method Methods 0.000 description 88
- 125000004494 ethyl ester group Chemical group 0.000 description 67
- -1 derivatives of 4-anilinoquinolinecarboxylic Chemical class 0.000 description 56
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 41
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 40
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 24
- 239000002253 acid Substances 0.000 description 23
- 238000002844 melting Methods 0.000 description 22
- 230000008018 melting Effects 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 21
- 150000002148 esters Chemical class 0.000 description 20
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 17
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 15
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 12
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 12
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 10
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 150000001448 anilines Chemical class 0.000 description 10
- 230000028327 secretion Effects 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 210000004051 gastric juice Anatomy 0.000 description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- 230000008569 process Effects 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 7
- 241000700159 Rattus Species 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 229960001340 histamine Drugs 0.000 description 6
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 6
- 235000011007 phosphoric acid Nutrition 0.000 description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- WBRPQQSADOCKCH-UHFFFAOYSA-N 2-methylsulfanylaniline Chemical compound CSC1=CC=CC=C1N WBRPQQSADOCKCH-UHFFFAOYSA-N 0.000 description 5
- 238000000921 elemental analysis Methods 0.000 description 5
- 239000012458 free base Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- VBLXCTYLWZJBKA-UHFFFAOYSA-N 2-(trifluoromethyl)aniline Chemical compound NC1=CC=CC=C1C(F)(F)F VBLXCTYLWZJBKA-UHFFFAOYSA-N 0.000 description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 4
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 4
- 239000010452 phosphate Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 3
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- VSXMSYVKRKWKDG-UHFFFAOYSA-N 3-ethyl-1,2-oxazol-5-amine Chemical compound CCC=1C=C(N)ON=1 VSXMSYVKRKWKDG-UHFFFAOYSA-N 0.000 description 3
- GCZKIAHUIXWOGS-UHFFFAOYSA-N 4-aminoquinoline-2-carboxylic acid Chemical class C1=CC=C2C(N)=CC(C(O)=O)=NC2=C1 GCZKIAHUIXWOGS-UHFFFAOYSA-N 0.000 description 3
- 241000282472 Canis lupus familiaris Species 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- 241000124008 Mammalia Species 0.000 description 3
- 208000008469 Peptic Ulcer Diseases 0.000 description 3
- 108010012944 Tetragastrin Proteins 0.000 description 3
- HCZHHEIFKROPDY-UHFFFAOYSA-N acide cynurenique Natural products C1=CC=C2NC(C(=O)O)=CC(=O)C2=C1 HCZHHEIFKROPDY-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 230000001262 anti-secretory effect Effects 0.000 description 3
- 230000000767 anti-ulcer Effects 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical class OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
- 210000002784 stomach Anatomy 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- RGYLYUZOGHTBRF-BIHRQFPBSA-N tetragastrin Chemical compound C([C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@@H](N)CC=1C2=CC=CC=C2NC=1)CCSC)C(N)=O)C1=CC=CC=C1 RGYLYUZOGHTBRF-BIHRQFPBSA-N 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- ULHFFAFDSSHFDA-UHFFFAOYSA-N 1-amino-2-ethoxybenzene Chemical compound CCOC1=CC=CC=C1N ULHFFAFDSSHFDA-UHFFFAOYSA-N 0.000 description 2
- CZZZABOKJQXEBO-UHFFFAOYSA-N 2,4-dimethylaniline Chemical compound CC1=CC=C(N)C(C)=C1 CZZZABOKJQXEBO-UHFFFAOYSA-N 0.000 description 2
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 2
- PXBFMLJZNCDSMP-UHFFFAOYSA-N 2-Aminobenzamide Chemical compound NC(=O)C1=CC=CC=C1N PXBFMLJZNCDSMP-UHFFFAOYSA-N 0.000 description 2
- HLCPWBZNUKCSBN-UHFFFAOYSA-N 2-aminobenzonitrile Chemical compound NC1=CC=CC=C1C#N HLCPWBZNUKCSBN-UHFFFAOYSA-N 0.000 description 2
- MLPVBIWIRCKMJV-UHFFFAOYSA-N 2-ethylaniline Chemical compound CCC1=CC=CC=C1N MLPVBIWIRCKMJV-UHFFFAOYSA-N 0.000 description 2
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
- XDHVXNYIJMSNIQ-UHFFFAOYSA-N 4-chloroquinoline-2-carboxylic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC(Cl)=C21 XDHVXNYIJMSNIQ-UHFFFAOYSA-N 0.000 description 2
- HJSCQRDGGJZGJH-UHFFFAOYSA-N 4-chloroquinoline-3-carboxylic acid Chemical compound C1=CC=CC2=C(Cl)C(C(=O)O)=CN=C21 HJSCQRDGGJZGJH-UHFFFAOYSA-N 0.000 description 2
- BASNAOYNNASHFC-UHFFFAOYSA-N 8-methoxy-4-(2-methylanilino)quinoline-3-carboxylic acid Chemical compound OC(=O)C1=CN=C2C(OC)=CC=CC2=C1NC1=CC=CC=C1C BASNAOYNNASHFC-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 150000003939 benzylamines Chemical class 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- HCYNWEIHLHVPEW-UHFFFAOYSA-N ethyl 8-methoxy-4-oxo-1h-quinoline-3-carboxylate Chemical compound C1=CC=C2C(=O)C(C(=O)OCC)=CNC2=C1OC HCYNWEIHLHVPEW-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
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- 210000004211 gastric acid Anatomy 0.000 description 2
- QMEZUZOCLYUADC-UHFFFAOYSA-N hydrate;dihydrochloride Chemical compound O.Cl.Cl QMEZUZOCLYUADC-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- CDGNLUSBENXDGG-UHFFFAOYSA-N meta-Cresidine Chemical compound COC1=CC=C(N)C(C)=C1 CDGNLUSBENXDGG-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
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- DJXNJVFEFSWHLY-UHFFFAOYSA-N quinoline-3-carboxylic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CN=C21 DJXNJVFEFSWHLY-UHFFFAOYSA-N 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
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- 238000012360 testing method Methods 0.000 description 2
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- CJAAPVQEZPAQNI-UHFFFAOYSA-N (2-methylphenyl)methanamine Chemical compound CC1=CC=CC=C1CN CJAAPVQEZPAQNI-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
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- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
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- 150000001340 alkali metals Chemical class 0.000 description 1
- VIROVYVQCGLCII-UHFFFAOYSA-N amobarbital Chemical group CC(C)CCC1(CC)C(=O)NC(=O)NC1=O VIROVYVQCGLCII-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- LTMHNWPUDSTBKD-UHFFFAOYSA-N diethyl 2-(ethoxymethylidene)propanedioate Chemical compound CCOC=C(C(=O)OCC)C(=O)OCC LTMHNWPUDSTBKD-UHFFFAOYSA-N 0.000 description 1
- 230000001079 digestive effect Effects 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical class CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 1
- FCZCIXQGZOUIDN-UHFFFAOYSA-N ethyl 2-diethoxyphosphinothioyloxyacetate Chemical compound CCOC(=O)COP(=S)(OCC)OCC FCZCIXQGZOUIDN-UHFFFAOYSA-N 0.000 description 1
- OCHKEQGEVIKLKP-UHFFFAOYSA-N ethyl 2-methoxyquinoline-3-carboxylate Chemical compound C1=CC=C2N=C(OC)C(C(=O)OCC)=CC2=C1 OCHKEQGEVIKLKP-UHFFFAOYSA-N 0.000 description 1
- HINLPSGAVZPTIW-UHFFFAOYSA-N ethyl 4,8-dichloroquinoline-3-carboxylate Chemical compound ClC1=CC=CC2=C(Cl)C(C(=O)OCC)=CN=C21 HINLPSGAVZPTIW-UHFFFAOYSA-N 0.000 description 1
- JVSKAUIBUCQZAR-UHFFFAOYSA-N ethyl 4-(2,6-dimethylanilino)-8-methoxyquinoline-3-carboxylate;hydrobromide Chemical compound Br.CCOC(=O)C1=CN=C2C(OC)=CC=CC2=C1NC1=C(C)C=CC=C1C JVSKAUIBUCQZAR-UHFFFAOYSA-N 0.000 description 1
- GMKXWJUQDZTZQH-UHFFFAOYSA-N ethyl 4-(2-acetylanilino)-8-methoxyquinoline-3-carboxylate;hydrochloride Chemical compound Cl.CCOC(=O)C1=CN=C2C(OC)=CC=CC2=C1NC1=CC=CC=C1C(C)=O GMKXWJUQDZTZQH-UHFFFAOYSA-N 0.000 description 1
- ZGIIOSQVHPDWCS-UHFFFAOYSA-N ethyl 4-(2-fluoroanilino)-8-methoxyquinoline-3-carboxylate;hydrochloride Chemical compound Cl.CCOC(=O)C1=CN=C2C(OC)=CC=CC2=C1NC1=CC=CC=C1F ZGIIOSQVHPDWCS-UHFFFAOYSA-N 0.000 description 1
- GFDXIDWCSMDKFQ-UHFFFAOYSA-N ethyl 4-(2-methoxyanilino)quinoline-3-carboxylate;hydrochloride Chemical compound Cl.CCOC(=O)C1=CN=C2C=CC=CC2=C1NC1=CC=CC=C1OC GFDXIDWCSMDKFQ-UHFFFAOYSA-N 0.000 description 1
- QVSYNWHRVQHXTG-UHFFFAOYSA-N ethyl 4-(2-methylanilino)quinoline-3-carboxylate;hydrochloride Chemical compound Cl.CCOC(=O)C1=CN=C2C=CC=CC2=C1NC1=CC=CC=C1C QVSYNWHRVQHXTG-UHFFFAOYSA-N 0.000 description 1
- LSBWFYVFLMJDSM-UHFFFAOYSA-N ethyl 4-(benzylamino)quinoline-3-carboxylate;hydrochloride Chemical compound Cl.CCOC(=O)C1=CN=C2C=CC=CC2=C1NCC1=CC=CC=C1 LSBWFYVFLMJDSM-UHFFFAOYSA-N 0.000 description 1
- DEFVNVNONGGPJR-UHFFFAOYSA-N ethyl 4-anilino-6,8-dimethylquinoline-3-carboxylate Chemical compound CCOC(=O)C1=CN=C2C(C)=CC(C)=CC2=C1NC1=CC=CC=C1 DEFVNVNONGGPJR-UHFFFAOYSA-N 0.000 description 1
- TZRPUJLDSWTXFE-UHFFFAOYSA-N ethyl 4-anilino-6-methoxyquinoline-3-carboxylate Chemical compound CCOC(=O)C1=CN=C2C=CC(OC)=CC2=C1NC1=CC=CC=C1 TZRPUJLDSWTXFE-UHFFFAOYSA-N 0.000 description 1
- YMSKONPFQZCVPL-UHFFFAOYSA-N ethyl 4-anilino-8-methoxyquinoline-3-carboxylate Chemical compound CCOC(=O)C1=CN=C2C(OC)=CC=CC2=C1NC1=CC=CC=C1 YMSKONPFQZCVPL-UHFFFAOYSA-N 0.000 description 1
- DGFFVGQOZXGJAE-UHFFFAOYSA-N ethyl 4-anilino-8-methoxyquinoline-3-carboxylate;hydrochloride Chemical compound Cl.CCOC(=O)C1=CN=C2C(OC)=CC=CC2=C1NC1=CC=CC=C1 DGFFVGQOZXGJAE-UHFFFAOYSA-N 0.000 description 1
- QOCJKSWVYYUBSD-UHFFFAOYSA-N ethyl 4-chloro-6,8-dimethylquinoline-3-carboxylate Chemical compound CC1=CC(C)=CC2=C(Cl)C(C(=O)OCC)=CN=C21 QOCJKSWVYYUBSD-UHFFFAOYSA-N 0.000 description 1
- IXMRUGGFGJIANG-UHFFFAOYSA-N ethyl 4-chloro-7-methoxyquinoline-3-carboxylate Chemical compound C1=C(OC)C=CC2=C(Cl)C(C(=O)OCC)=CN=C21 IXMRUGGFGJIANG-UHFFFAOYSA-N 0.000 description 1
- MHOFAUCLSGVKOH-UHFFFAOYSA-N ethyl 4-chloro-8-cyanoquinoline-3-carboxylate Chemical compound N#CC1=CC=CC2=C(Cl)C(C(=O)OCC)=CN=C21 MHOFAUCLSGVKOH-UHFFFAOYSA-N 0.000 description 1
- UNMTVPUUJFYTOJ-UHFFFAOYSA-N ethyl 4-chloro-8-ethoxyquinoline-3-carboxylate Chemical compound CCOC1=CC=CC2=C(Cl)C(C(=O)OCC)=CN=C21 UNMTVPUUJFYTOJ-UHFFFAOYSA-N 0.000 description 1
- BBOZDELEERNECG-UHFFFAOYSA-N ethyl 4-chloro-8-methoxyquinoline-3-carboxylate Chemical compound COC1=CC=CC2=C(Cl)C(C(=O)OCC)=CN=C21 BBOZDELEERNECG-UHFFFAOYSA-N 0.000 description 1
- PGGVUZUNDXCMSS-UHFFFAOYSA-N ethyl 4-chloro-8-methylquinoline-3-carboxylate Chemical compound CC1=CC=CC2=C(Cl)C(C(=O)OCC)=CN=C21 PGGVUZUNDXCMSS-UHFFFAOYSA-N 0.000 description 1
- DWXQUAHMZWZXHP-UHFFFAOYSA-N ethyl 4-chloroquinoline-3-carboxylate Chemical compound C1=CC=CC2=C(Cl)C(C(=O)OCC)=CN=C21 DWXQUAHMZWZXHP-UHFFFAOYSA-N 0.000 description 1
- YBEOYBKKSWUSBR-UHFFFAOYSA-N ethyl 4-oxo-1h-quinoline-3-carboxylate Chemical compound C1=CC=C2C(=O)C(C(=O)OCC)=CNC2=C1 YBEOYBKKSWUSBR-UHFFFAOYSA-N 0.000 description 1
- IRKHEJCWIWBURM-UHFFFAOYSA-N ethyl 4-oxo-8-phenyl-1h-quinoline-3-carboxylate Chemical compound C1=CC=C2C(=O)C(C(=O)OCC)=CNC2=C1C1=CC=CC=C1 IRKHEJCWIWBURM-UHFFFAOYSA-N 0.000 description 1
- ZFOVQQHLWOBEKQ-UHFFFAOYSA-N ethyl 5,8-dimethoxy-4-oxo-1h-quinoline-3-carboxylate Chemical compound C1=CC(OC)=C2C(=O)C(C(=O)OCC)=CNC2=C1OC ZFOVQQHLWOBEKQ-UHFFFAOYSA-N 0.000 description 1
- MHONKQIXMNJTGY-UHFFFAOYSA-N ethyl 7-methoxyquinoline-3-carboxylate Chemical compound C1=C(OC)C=CC2=CC(C(=O)OCC)=CN=C21 MHONKQIXMNJTGY-UHFFFAOYSA-N 0.000 description 1
- IOXBKBFKCYONPW-UHFFFAOYSA-N ethyl 8-cyano-4-oxo-1h-quinoline-3-carboxylate Chemical compound C1=CC=C2C(=O)C(C(=O)OCC)=CNC2=C1C#N IOXBKBFKCYONPW-UHFFFAOYSA-N 0.000 description 1
- NPHTWWPHPYENDB-UHFFFAOYSA-N ethyl 8-methoxy-5-methyl-4-(2-methylanilino)quinoline-3-carboxylate Chemical compound CCOC(=O)C1=CN=C2C(OC)=CC=C(C)C2=C1NC1=CC=CC=C1C NPHTWWPHPYENDB-UHFFFAOYSA-N 0.000 description 1
- HYUYDOCMASKUMM-UHFFFAOYSA-N ethyl 8-methyl-4-oxo-1h-quinoline-3-carboxylate Chemical compound C1=CC=C2C(=O)C(C(=O)OCC)=CNC2=C1C HYUYDOCMASKUMM-UHFFFAOYSA-N 0.000 description 1
- ZJXZSIYSNXKHEA-UHFFFAOYSA-N ethyl dihydrogen phosphate Chemical compound CCOP(O)(O)=O ZJXZSIYSNXKHEA-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- DBEYVIGIPJSTOR-FHWLQOOXSA-N fumitremorgin C Chemical compound O=C1[C@@H]2CCCN2C(=O)[C@@H]2CC(C3=CC=C(C=C3N3)OC)=C3[C@H](C=C(C)C)N21 DBEYVIGIPJSTOR-FHWLQOOXSA-N 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 210000001156 gastric mucosa Anatomy 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- KEBXGLIHHLGNJH-UHFFFAOYSA-N n-methylsulfanylaniline Chemical compound CSNC1=CC=CC=C1 KEBXGLIHHLGNJH-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000024717 negative regulation of secretion Effects 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- WXWCDTXEKCVRRO-UHFFFAOYSA-N para-Cresidine Chemical compound COC1=CC=C(C)C=C1N WXWCDTXEKCVRRO-UHFFFAOYSA-N 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 1
- KVROVDQWRUAIID-UHFFFAOYSA-N quinoline-3-carboxylic acid;hydrochloride Chemical compound Cl.C1=CC=CC2=CC(C(=O)O)=CN=C21 KVROVDQWRUAIID-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 230000036269 ulceration Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2398179A | 1979-03-26 | 1979-03-26 | |
| US06/127,153 US4343804A (en) | 1979-03-26 | 1980-03-04 | 4-Amino-3-quinolinecarboxylic acids and esters-antisecretory anti-ulcer compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL222993A1 PL222993A1 (ru) | 1981-01-30 |
| PL125030B1 true PL125030B1 (en) | 1983-03-31 |
Family
ID=26697875
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1980222993A PL125030B1 (en) | 1979-03-26 | 1980-03-25 | Method of manufacture of novel derivatives of 4-aminoquinoline-3-carboxylic acid |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US4343804A (ru) |
| JP (1) | JPH02117663A (ru) |
| AR (1) | AR230268A1 (ru) |
| AT (1) | AT372373B (ru) |
| AU (1) | AU528388B2 (ru) |
| BR (1) | BR8001779A (ru) |
| CA (1) | CA1147338A (ru) |
| CH (1) | CH644105A5 (ru) |
| DE (1) | DE3011490A1 (ru) |
| DK (1) | DK156056C (ru) |
| EG (1) | EG15009A (ru) |
| ES (1) | ES489887A0 (ru) |
| FI (1) | FI77452C (ru) |
| FR (1) | FR2452485B1 (ru) |
| GB (1) | GB2047244B (ru) |
| GR (1) | GR68006B (ru) |
| HK (1) | HK67983A (ru) |
| IE (1) | IE49577B1 (ru) |
| IL (1) | IL59628A (ru) |
| IN (1) | IN151446B (ru) |
| IT (1) | IT1133079B (ru) |
| MX (1) | MX6264E (ru) |
| NL (1) | NL8001752A (ru) |
| NO (1) | NO153927C (ru) |
| NZ (1) | NZ193252A (ru) |
| PH (1) | PH16416A (ru) |
| PL (1) | PL125030B1 (ru) |
| PT (1) | PT71008B (ru) |
| SE (1) | SE435837B (ru) |
| SG (1) | SG33683G (ru) |
| YU (1) | YU41702B (ru) |
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8610981D0 (en) * | 1986-05-06 | 1986-06-11 | Ici America Inc | Quinoline amides |
| GB8621425D0 (en) * | 1986-09-05 | 1986-10-15 | Smith Kline French Lab | Compounds |
| GB8804446D0 (en) * | 1988-02-25 | 1988-03-23 | Smithkline Beckman Intercredit | Compounds |
| GB8804443D0 (en) * | 1988-02-25 | 1988-03-23 | Smithkline Beckman Intercredit | Compounds |
| GB8804448D0 (en) * | 1988-02-25 | 1988-03-23 | Smithkline Beckman Intercredit | Compounds |
| GB8804445D0 (en) * | 1988-02-25 | 1988-03-23 | Smithkline Beckman Intercredit | Compounds |
| GB8804444D0 (en) * | 1988-02-25 | 1988-03-23 | Smithkline Beckman Intercredit | Compounds |
| GB8804447D0 (en) * | 1988-02-25 | 1988-03-23 | Smithkline Beckman Intercredit | Compounds |
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| DE3917233A1 (de) * | 1989-05-26 | 1990-11-29 | Basf Ag | 8-substituierte 4-(heterocyclylmethylamino)-chinoline, ihre verwendung und daraus hergestellte arzneimittel |
| GB8918265D0 (en) * | 1989-08-10 | 1989-09-20 | Smithkline Beckman Intercredit | Compounds |
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| BR9914164A (pt) | 1998-09-29 | 2001-06-26 | American Cyanamid Co | Composto, método para o tratamento, inibição do crescimento de, ou erradiacação de um neoplasma, e de doença de rim policìstico, em um mamìfero em necessidade do mesmo, composição farmacêutica, e, processo para preparar um composto |
| MXPA02006474A (es) * | 1999-12-28 | 2002-11-29 | Eisai Co Ltd | Compuestos heterociclicos que contienen sulfonamida. |
| US6521618B2 (en) | 2000-03-28 | 2003-02-18 | Wyeth | 3-cyanoquinolines, 3-cyano-1,6-naphthyridines, and 3-cyano-1,7-naphthyridines as protein kinase inhibitors |
| US6576644B2 (en) * | 2000-09-06 | 2003-06-10 | Bristol-Myers Squibb Co. | Quinoline inhibitors of cGMP phosphodiesterase |
| UA80393C2 (ru) | 2000-12-07 | 2007-09-25 | Алтана Фарма Аг | Фармацевтическая композиция, которая содержит ингибитор фдэ 4, диспергированный в матрице |
| MY140561A (en) | 2002-02-20 | 2009-12-31 | Nycomed Gmbh | Dosage form containing pde 4 inhibitor as active ingredient |
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| ME00524B (me) | 2003-03-10 | 2011-10-10 | Astrazeneca Ab | Novi postupak za dobijanje roflumilasta |
| WO2005007658A2 (en) * | 2003-07-14 | 2005-01-27 | Arena Pharmaceuticals, Inc. | Fused-aryl and heteroaryl derivatives as modulators of metabolism and the prophylaxis and treatment of disorders related thereto |
| CA2601250C (en) * | 2005-03-16 | 2014-10-28 | Nycomed Gmbh | Taste masked dosage form containing roflumilast |
| WO2011022216A1 (en) * | 2009-08-17 | 2011-02-24 | High Point Pharmaceuticals, Llc | Substituted pyridine derivatives, pharmaceutical compositions, and methods of use to treat oxidative stress |
| EP3378854B1 (en) | 2010-01-27 | 2022-12-21 | Arena Pharmaceuticals, Inc. | Processes for the preparation of (r)-2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid and salts thereof |
| BR112013008100A2 (pt) | 2010-09-22 | 2016-08-09 | Arena Pharm Inc | "moduladores do receptor de gpr19 e o tratamento de distúrbios relacionados a eles." |
| CN116850181A (zh) | 2015-01-06 | 2023-10-10 | 艾尼纳制药公司 | 治疗与s1p1受体有关的病症的方法 |
| MX2017016530A (es) | 2015-06-22 | 2018-03-12 | Arena Pharm Inc | Sal cristalina de l-arginina del acido (r)-2-(7-(4-ciclopentil-3-( trifluorometil)benciloxi)-1,2,3,4-tetrahidrociclopenta[b]indol-3- il)acetico (compuesto1) para ser utilizada en transtornos asociados con el receptor de esfingosina-1-fosfato 1 (s1p1). |
| ES2884073T3 (es) * | 2016-11-11 | 2021-12-10 | Bayer Animal Health Gmbh | Nuevos derivados antihelmínticos de quinolina-3-carboxamida |
| CN110520124A (zh) | 2017-02-16 | 2019-11-29 | 艾尼纳制药公司 | 用于治疗原发性胆汁性胆管炎的化合物和方法 |
| EP3700527A4 (en) * | 2017-10-25 | 2021-03-10 | Children's Medical Center Corporation | PAPD5 INHIBITORS AND THEIR METHODS OF USE |
| WO2019215182A1 (en) | 2018-05-09 | 2019-11-14 | Bayer Animal Health Gmbh | New quinoline derivatives |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3470186A (en) * | 1967-06-02 | 1969-09-30 | American Cyanamid Co | Substituted 4-anilino-3-quinolinecarboxylic acids and esters |
| JPS4838712A (ru) * | 1971-09-18 | 1973-06-07 |
-
1980
- 1980-03-04 US US06/127,153 patent/US4343804A/en not_active Expired - Lifetime
- 1980-03-14 IL IL59628A patent/IL59628A/xx unknown
- 1980-03-22 GR GR61513A patent/GR68006B/el unknown
- 1980-03-24 MX MX808722U patent/MX6264E/es unknown
- 1980-03-24 IE IE605/80A patent/IE49577B1/en unknown
- 1980-03-24 FI FI800910A patent/FI77452C/fi not_active IP Right Cessation
- 1980-03-24 AT AT0156480A patent/AT372373B/de not_active IP Right Cessation
- 1980-03-24 FR FR8006516A patent/FR2452485B1/fr not_active Expired
- 1980-03-25 GB GB8009991A patent/GB2047244B/en not_active Expired
- 1980-03-25 IN IN345/CAL/80A patent/IN151446B/en unknown
- 1980-03-25 EG EG80174A patent/EG15009A/xx active
- 1980-03-25 DE DE19803011490 patent/DE3011490A1/de active Granted
- 1980-03-25 NL NL8001752A patent/NL8001752A/nl not_active Application Discontinuation
- 1980-03-25 PT PT71008A patent/PT71008B/pt unknown
- 1980-03-25 ES ES489887A patent/ES489887A0/es active Granted
- 1980-03-25 SE SE8002292A patent/SE435837B/sv not_active IP Right Cessation
- 1980-03-25 BR BR8001779A patent/BR8001779A/pt unknown
- 1980-03-25 NO NO800858A patent/NO153927C/no unknown
- 1980-03-25 PH PH23804A patent/PH16416A/en unknown
- 1980-03-25 PL PL1980222993A patent/PL125030B1/pl unknown
- 1980-03-25 NZ NZ193252A patent/NZ193252A/en unknown
- 1980-03-25 CH CH234080A patent/CH644105A5/fr not_active IP Right Cessation
- 1980-03-25 DK DK128380A patent/DK156056C/da not_active IP Right Cessation
- 1980-03-26 AU AU56848/80A patent/AU528388B2/en not_active Ceased
- 1980-03-26 AR AR280455A patent/AR230268A1/es active
- 1980-03-26 CA CA000348417A patent/CA1147338A/en not_active Expired
- 1980-03-26 YU YU844/80A patent/YU41702B/xx unknown
- 1980-03-26 IT IT67465/80A patent/IT1133079B/it active
-
1983
- 1983-06-13 SG SG336/83A patent/SG33683G/en unknown
- 1983-12-15 HK HK679/83A patent/HK67983A/xx unknown
-
1989
- 1989-09-26 JP JP1250369A patent/JPH02117663A/ja active Pending
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